diff --git a/ktor-client/ktor-client-core/common/src/io/ktor/client/plugins/HttpRequestRetry.kt b/ktor-client/ktor-client-core/common/src/io/ktor/client/plugins/HttpRequestRetry.kt
index 2f042909db6..7a36e5b6f49 100644
--- a/ktor-client/ktor-client-core/common/src/io/ktor/client/plugins/HttpRequestRetry.kt
+++ b/ktor-client/ktor-client-core/common/src/io/ktor/client/plugins/HttpRequestRetry.kt
@@ -6,8 +6,10 @@ package io.ktor.client.plugins
 
 import io.ktor.client.*
 import io.ktor.client.call.*
+import io.ktor.client.network.sockets.*
 import io.ktor.client.request.*
 import io.ktor.client.statement.*
+import io.ktor.client.utils.*
 import io.ktor.events.*
 import io.ktor.http.*
 import io.ktor.util.*
@@ -167,14 +169,16 @@ public class HttpRequestRetry internal constructor(configuration: Configuration)
         /**
          * Enables retrying a request if an exception is thrown during the [HttpSend] phase
          * and specifies the number of retries.
-         * By default, [HttpRequestTimeoutException] is not retried. Set [retryOnTimeout] to `true` to retry on timeout.
+         * By default, [HttpRequestTimeoutException], [ConnectTimeoutException] and [SocketTimeoutException]
+         * are not retried.
+         * Set [retryOnTimeout] to `true` to retry on timeout.
          * Note, that in this case, [HttpTimeout] plugin should be installed after [HttpRequestRetry].
          */
         public fun retryOnException(maxRetries: Int = -1, retryOnTimeout: Boolean = false) {
             retryOnExceptionIf(maxRetries) { _, cause ->
                 when {
+                    cause.isTimeoutException() -> retryOnTimeout
                     cause is CancellationException -> false
-                    cause is HttpRequestTimeoutException && retryOnTimeout -> true
                     else -> true
                 }
             }
@@ -392,3 +396,10 @@ private val RetryDelayPerRequestAttributeKey =
     AttributeKey<HttpRequestRetry.DelayContext.(Int) -> Long>(
         "RetryDelayPerRequestAttributeKey"
     )
+
+private fun Throwable.isTimeoutException(): Boolean {
+    val exception = unwrapCancellationException()
+    return exception is HttpRequestTimeoutException ||
+        exception is ConnectTimeoutException ||
+        exception is SocketTimeoutException
+}
diff --git a/ktor-client/ktor-client-core/js/src/io/ktor/client/utils/ExceptionUtilsJs.kt b/ktor-client/ktor-client-core/js/src/io/ktor/client/utils/ExceptionUtilsJs.kt
index 237ad648850..2f01ecee8ba 100644
--- a/ktor-client/ktor-client-core/js/src/io/ktor/client/utils/ExceptionUtilsJs.kt
+++ b/ktor-client/ktor-client-core/js/src/io/ktor/client/utils/ExceptionUtilsJs.kt
@@ -9,4 +9,15 @@ import io.ktor.utils.io.*
 /**
  * If the exception contains cause that differs from [CancellationException] returns it otherwise returns itself.
  */
-public actual fun Throwable.unwrapCancellationException(): Throwable = this
+public actual fun Throwable.unwrapCancellationException(): Throwable {
+    var exception: Throwable? = this
+    while (exception is CancellationException) {
+        // If there is a cycle, we return the initial exception.
+        if (exception == exception.cause) {
+            return this
+        }
+        exception = exception.cause
+    }
+
+    return exception ?: this
+}
diff --git a/ktor-client/ktor-client-tests/common/test/io/ktor/client/tests/HttpRequestRetryTest.kt b/ktor-client/ktor-client-tests/common/test/io/ktor/client/tests/HttpRequestRetryTest.kt
index 2ef322bd577..4c3d7b13e61 100644
--- a/ktor-client/ktor-client-tests/common/test/io/ktor/client/tests/HttpRequestRetryTest.kt
+++ b/ktor-client/ktor-client-tests/common/test/io/ktor/client/tests/HttpRequestRetryTest.kt
@@ -408,9 +408,8 @@ class HttpRequestRetryTest {
         }
 
         test { client ->
-            assertFailsWith<HttpRequestTimeoutException> {
-                client.get {}
-            }
+            val response = client.get {}
+            assertEquals(HttpStatusCode.OK, response.status)
         }
     }
 }
diff --git a/ktor-server/ktor-server-core/jvmAndNix/src/io/ktor/server/routing/RoutingResolveContext.kt b/ktor-server/ktor-server-core/jvmAndNix/src/io/ktor/server/routing/RoutingResolveContext.kt
index 25eee305b1c..3f6f12feb9b 100644
--- a/ktor-server/ktor-server-core/jvmAndNix/src/io/ktor/server/routing/RoutingResolveContext.kt
+++ b/ktor-server/ktor-server-core/jvmAndNix/src/io/ktor/server/routing/RoutingResolveContext.kt
@@ -231,8 +231,8 @@ public class RoutingResolveContext(
         trait: ArrayList<RoutingResolveResult.Success>
     ) {
         val current = failedEvaluation ?: return
-        if ((current.quality < new.quality || failedEvaluationDepth < trait.size)
-            && trait.all {
+        if ((current.quality < new.quality || failedEvaluationDepth < trait.size) &&
+            trait.all {
                 it.quality == RouteSelectorEvaluation.qualityTransparent ||
                     it.quality == RouteSelectorEvaluation.qualityConstant
             }